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Cas Database |
| Name |
1-Adamantanol |
EINECS | 212-202-8 |
| CAS No. | 768-95-6 | Density | 1.16 g/cm3 |
| PSA | 20.23000 | LogP | 1.94750 |
| Solubility | Soluble in ethanol , methanol, and diethyl ether. Partly miscible in water. | Melting Point |
247 °C (subl.)(lit.) |
| Formula | C10H16O | Boiling Point | 245.8 °C at 760 mmHg |
| Molecular Weight | 152.236 | Flash Point | 101.131 °C |
| Transport Information | N/A | Appearance | white to off-white crystalline powder or needles |
| Safety | 22-24/25-36-26 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi
|
| Synonyms |
Tricyclo(3.3.1.1(sup 3,7))decan-1-ol (9CI);1-Adamantol;Tricyclo[3.3.1.13,7]decan-1-ol;Adapalene-1;1-Ad-OH;Tricyclo(3.3.1.13,7)decan-1-ol;1-Hydroxyadamantane;adamantan-1-ol;tricyclo[3.3.1.1~3,7~]decan-1-ol; |
Article Data | 460 |
1-Adamantanol Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| With tert-butyldibutyltin chloride; sodium cyanoborohydride In tert-butyl alcohol at 33℃; for 18h; Ultrasound with 20 KHz and bubbling of air; | 100% |
| With 2,2'-azobis(isobutyronitrile); PVS; N-ethylpiperidinium hypophosphite In 1,4-dioxane; water at 100℃; for 0.5h; | 72% |
| With PVS; (CH3)3N(+)(CH2)15CH3*H2PO2(-); 4,4'-dicyano-4,4'-azo-di-valeric acid In water at 100℃; for 1h; | 70% |
Conditions
| Conditions | Yield |
|---|---|
| With Fe(AAEMA)3; oxygen; isovaleraldehyde In 1,2-dichloro-ethane under 760 Torr; for 60h; Ambient temperature; | 99% |
| With oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; under 3878.71 Torr; for 0.0222222h; Reagent/catalyst; Temperature; Solvent; | 99% |
| With water; bromine for 1h; Ambient temperature; | 95% |
Conditions
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; oxygen; caesium carbonate In dichloromethane at 40℃; for 40h; Irradiation; | 99% |
| With manganese(IV) oxide; sulfuric acid at 25 - 30℃; | 82% |
| Stage #1: 1-Adamantanecarboxylic acid With dipotassium hydrogenphosphate; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In chloroform at 20℃; for 48h; Schlenk technique; Irradiation; Green chemistry; Stage #2: With sodium tetrahydroborate In methanol; chloroform for 0.5h; Green chemistry; | 40% |
- 88773-89-1
2-(tricyclo[3.3.1.13,7]dec-1-yloxy)tetrahydro-2H-pyran
- 768-95-6
1-adamanthanol
Conditions
| Conditions | Yield |
|---|---|
| poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 50h; Hydrolysis; | 99% |
| With 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; water for 1h; Ambient temperature; | 96% |
| With methanol at 20℃; for 0.666667h; | 92% |
- 36960-53-9
1-trimethylsiloxyadamantane
- 768-95-6
1-adamanthanol
Conditions
| Conditions | Yield |
|---|---|
| With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.1h; Green chemistry; | 99% |
| With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.333333h; | 96% |
| With silicaphosphite (silphos), [PCl3-n(SiO2)n] In acetonitrile at 20℃; for 0.0333333h; | 95% |
Conditions
| Conditions | Yield |
|---|---|
| With tetra-(n-butyl)ammonium iodide In acetic anhydride; acetic acid; N,N-dimethyl-formamide at 0 - 10℃; for 4h; Substitution; Electrochemical reaction; | 98% |
| With water; bromine for 1h; | 95.5% |
| With hydrogenchloride In N,N-dimethyl-formamide at 105℃; for 0.5h; | 95% |
Conditions
| Conditions | Yield |
|---|---|
| With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Product distribution; | A n/a B 97% C n/a |
| With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Yields of byproduct given; | A n/a B 97% C n/a |
| With ammonium cerium(IV) nitrate; oxygen In acetonitrile for 5h; Ambient temperature; Irradiation; | A 5% B 85% C 5% |
- 768-95-6
1-adamanthanol
Conditions
| Conditions | Yield |
|---|---|
| With ytterbium(III) triflate In methanol at 50℃; for 36h; | 97% |
Conditions
| Conditions | Yield |
|---|---|
| With 2,2'-azobis(isobutyronitrile); oxygen; tert-butyldibutyltin chloride; sodium cyanoborohydride In tert-butyl alcohol at 60℃; for 20h; Yields of byproduct given; | A n/a B 96% |
| With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction; | A 42% B n/a |
- 76358-85-5
1-(tert-butyldimethylsiloxy)tricyclo[3.3.1.1]decane
- 768-95-6
1-adamanthanol
Conditions
| Conditions | Yield |
|---|---|
| With 2,5-bis(perfluorohexyl)-3,6-dichloro-1,4-benzoquinone In water; acetonitrile at 50℃; for 6h; | 96% |
| With N-iodo-succinimide In methanol at 20℃; for 24h; | 69% |
| sulfonic acid functionalized nanoporous silica In methanol at 35℃; for 24h; | 50 % Chromat. |
1-Adamantanol Specification
1. Introduction of 1-Adamantanol
1-Adamantanol is also called Tricyclo[3.3.1.1(3,7)]decan-1-ol ; Tricyclo[3.3.1.1]decan-1-ol ; 1-Adamantol ; 1-Adamatanol ; Damantol-(1) ; Tricyclo(3.3.1.1(sup3,7))decan-1-ol ; 1-Hydroxydiamantane.
2. Properties of 1-Adamantanol
Melting Point: 247 °C (subl.)(lit.)
Flash Point: 240°C
Boiling Point: 245.8 °C at 760 mmHg
Freely Rotating Bonds: 1
Polar Surface Area: 9.23 Å2
Index of Refraction: 1.58
Molar Refractivity: 43.71 cm3
Molar Volume: 131.1 cm3
Surface Tension: 49.3 dyne/cm
Enthalpy of Vaporization: 56.11 kJ/mol
Vapour Pressure: 0.00466 mmHg at 25°C
Appearance: white to off-white crystalline powder or needles
3. Structure Descriptors of 1-Adamantanol
InChI=1S/C10H16O/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9,11H,1-6H2
4. Toxicity of 1-Adamantanol
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 600mg/kg (600mg/kg) | Pharmaceutical Chemistry Journal Vol. 10, Pg. 454, 1976. |
5. Safety Information of 1-Adamantanol
Hazard Codes:
Xi Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S36: Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: AU4980000
Hazard Note: Irritant
HS Code: 29061900
6. Use of 1-Adamantanol
1-Adamantanol is used to make adamantane derivatives and adapalene.
7. Storage and transportation of 1-Adamantanol
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Avoid to contact water or moisture during storing and transporting.
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